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Jess Redmon

@itsjessredmon

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3 months ago

Apparently if I’m going to keep showing up on the internet, I should probably introduce myself. 👋

The funny thing is, I’ve spent most of my career helping other brands with visibility. Being the one on this side of the camera is still a little uncomfortable.

But I’m here for it.

I’ll be talking mostly about branding, creativity, building a business, why boring is usually a choice, and whatever else I’m thinking about loudly enough to make a Reel about.

There will probably also be some mom fails, hiking, live music, Nashville, drives in my ’78 Scout, strong opinions about design, and evidence that I will voluntarily sign up for almost any hard thing.

If any of that sounds like your kind of thing, 👋. I’m Jess. Glad you’re here. 🫶🏻 taken in Franklin, Tennessee by @itsjessredmon

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3 days ago

That itchy shirt tag? Felt it.
That side-eye she didn’t think you noticed? Caught it.
The temperature dropping by one degree? Sensed it.

Being sensitive is a trait I’ve often wished I could dial down.

But after two decades in the field of design, I’ve learned that the difference between good work and great work often lives in the details others may overlook.

And here’s where it gets interesting.

Research has found a relationship between sensitivity, creativity, and empathy. Which makes me wonder if we’ve been thinking about sensitivity all wrong.

Because sensitivity is a trait. Discernment is a skill.

Sensitivity helps us notice the subtleties. Experience teaches us how to interpret them. And practice teaches us what to do with what we notice.

That’s discernment. And it’s something we can apply professionally.

As AI makes it easier for anyone to create almost anything, I’m becoming less concerned about who can make the thing.

I’m more interested in who knows whether the thing is worth making.

Maybe the sensitivity we’ve spent our lives trying to dial down is something we should be learning to develop into our greatest professional advantage.

Episode 3 of Will We Be Obsolete:
I’m curious, fellow creatives: Has your sensitivity ever felt like both a blessing and a curse?

Research: Relationships of Sensory Processing Sensitivity with Creativity and Empathy in an Adult Sample (2025), Frontiers in Psychology.

#WillWeBeObsolete #CreativeThinking #DesignThinking #ArtificialIntelligence #Creativity taken in Franklin, Tennessee by @itsjessredmon

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4 days ago

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8 days ago

Tonight I’m speaking on a panel about avoiding year-end burnout.

Which is hilarious, because I’m not entirely sure I’ve ever successfully avoided it. 😅

Q4 has this sneaky way of convincing us that EVERYTHING needs to happen before December 31: finish the projects, hit the goals, make the plans, attend the things, buy the gifts, create the memories, somehow maintain a functioning household… and maybe workout occasionally?

So instead of showing up tonight pretending I have the answers, I want to bring some of yours with me.

What actually helps YOU avoid the end-of-year crash?

A boundary you set?
Something you stop doing?
A ritual that keeps you sane?
A lesson you learned the hard way?

Drop it in the comments. 👇

I’m taking notes before tonight’s panel at The Sanctuary Golf & Social Club! I have no doubt the collective wisdom here is going to be better than anything I could come up with on my own. 🙏

#Burnout #Leadership #Entrepreneurship #CreativeLeadership #FounderLife taken in Franklin, Tennessee by @itsjessredmon

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11 days ago

Here’s some well designed things I’ve been inspired by lately:

Creamy and dreamy cake batter packaging 🤤

Thor showing off at Cracker Barrel 🌩️

I’m down for UP-UP chocolate bars

“Go ahead and keep painting letters right across those windows.”

Smokin’ hand painted sign

The table is dirty but the vibes are right.

Mother Nature always wins this contest. 🦋

Unicorn of the sea illustrated letterpress card (and helpful reminder)

Pumpkin spicy arrangement @thesteelponytn.

At the end of a long day, give me this. @drinkmedly

Farmers market fall florals by @southernflorafarms taken in Franklin, Tennessee by @itsjessredmon

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12 days ago

Last episode, I ended with a question: What happens to us?

I’m starting to think answering it requires us to ask some harder questions about what it actually means to create.

If the idea is mine, but the execution is AI’s, am I still the creator?

Is creativity the idea, or the act of bringing it to life?

Does mastery of a craft matter if you can get to the same result without it?

Are the years of failed attempts and hours toiling in Illustrator inefficiencies we should be thrilled to eliminate?

Or are they part of what gives the work meaning?

And if we decide that the idea is what makes someone a creator… what happens when everyone suddenly has the ability to execute every idea?

I don’t think we can answer “What happens to us?” until we figure out what we believe still belongs to us.

So, pick a side:

If AI did the making, did you still create it?

#WillWeBeObsolete #AIAndCreativity #FutureOfCreativity #HumanCreativity #DesignThinking taken in Franklin, Tennessee by @itsjessredmon

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16 days ago

I used AI to write the first version of this reel.

It was about why I love driving my ’78 Scout. The wind, the music, the open road, etc.

It was true. And benign.

I posted it as a Trial and it did exactly what you’d expect.

Absolutely nothing.

So I tried again.

Except this time, I said the deeper, rawer truth underneath the truth.

And in doing that, I probably repelled some people and drew others closer.

Because almost no one feels strongly about something designed to appeal to everyone.

And I think the same thing is happening to brands.

The strongest ones today aren’t watering themselves down for mass appeal.

They know who they’re talking to, speak directly to them, and have the conviction to be clear about who they are and what they believe.

That clarity won’t resonate with everyone.

By design.

The most memorable brands make us feel something.

So when I say “you’re too likeable,” I don’t mean you should try to piss people off.

I mean: if everything you say is polished, agreeable and universally palatable, you’ve probably sanded off everything that makes you worth choosing.

Being disliked isn’t the problem.

Being forgettable is. taken in Franklin, Tennessee by @itsjessredmon

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18 days ago

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19 days ago

I’m spending the next few weeks exploring what happens to designers when the ability to make things is no longer the scarce skill.

I have some theories. I definitely don’t have all the answers.

Come figure it out with me.

#WillWeBeObsolete #Designers #DesignIndustry #FutureOfDesign #CreativeIndustry taken in Franklin, Tennessee by @itsjessredmon

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24 days ago